Potassium Carbonate → 6-Fluoro-1-(3-fluoro-2-methylphenyl)-8-methoxy-3,4-dimethylimidazo[1,5-a]quinoxaline

HRID 254308Notes

Reaction equation

HRID 254308 reaction equation
Br[C:2]1[N:6]2[C:7]3[C:12]([N:13]=[C:14]([CH3:15])[C:5]2=[C:4]([CH3:19])[N:3]=1)=[C:11]([F:16])[CH:10]=[C:9]([O:17][CH3:18])[CH:8]=3.[F:20][C:21]1[C:22]([CH3:30])=[C:23](B(O)O)[CH:24]=[CH:25][CH:26]=1.C([O-])([O-])=O.[K+].[K+]>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[F:16][C:11]1[CH:10]=[C:9]([O:17][CH3:18])[CH:8]=[C:7]2[C:12]=1[N:13]=[C:14]([CH3:15])[C:5]1[N:6]2[C:2]([C:23]2[CH:24]=[CH:25][CH:26]=[C:21]([F:20])[C:22]=2[CH3:30])=[N:3][C:4]=1[CH3:19]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 27831913-Fluoro-2-methylphenylboronic AcidHCID 577324641-Bromo-6-fluoro-8-methoxy-3,4-dimethylimidazo[1,5-a]quinoxaline

Product 1

HCID 426294756-Fluoro-1-(3-fluoro-2-methylphenyl)-8-methoxy-3,4-dimethylimidazo[1,5-a]quinoxalineYield 43%

Reagents, catalysts & solvents 1

HCID 178418397HCID 178418397, compoundCatalyst

Procedure

Following the general Suzuki coupling procedure, reaction of bromide 6A (65 mg, 0.2 mmol), 3-fluoro-2-methylphenylboronic acid (46 mg, 0.3 mmol), K2CO3 (82 mg, 0.6 mmol) and Pd(PPh3)4 (5 mg, 0.004 mmol) provided the coupling product as an off-white powder (30 mg, 43% yield). EIMS 354.1 [M+H]+.

Sources & evidence

ORD record
ord-fb16613493934b6e96f60d5fdb57a117
Source dataset
uspto-grants-2011_01
Patent number
US07875618B2

Reaction notes

Loading…